Who Said Failure was Fashionable? Frankly, It Sucks.

Howard Tullman is the CEO of Chicago-based 1871, where, at the moment, 260 digital startups are building their businesses every day. He is also the general managing partner of G2T3V and Chicago High Tech Investors--both early-stage venture funds; a member of Mayor Emanuel’s ChicagoNEXT Innovation Council; and Governor Quinn’s Illinois Innovation Council. He is an adviser to many technology businesses and an adjunct professor at the Kellogg Graduate School of Management. @tullman

Somehow, it has become cool to brag about how your last business failed--and what a wonderful learning experience it all was. But that’s a crock. You only fail when you give up, and giving up is something that winners never do. In my opinion, only cretins celebrate their failures.

Making mistakes, on the other hand, is something you have to do from time to time. It’s a sign of a healthy, active and risk-taking business. Mistakes are a critical part of growing and expanding your company and, if you’re not stubbing your toe from time to time, you’re not pushing forward. Rapid growth and constantly changing circumstances are inherently embarrassing - you need to get used to it. A thick skin helps a lot in a start-up.

When I was starting out, several VCs told me that they never invest in businesses founded by lawyers because too many lawyers are more concerned about being “right” than about doing what’s right for the business. They’d rather die than die of embarrassment. But being smart doesn’t mean that you make only good decisions. It means that you learn from your bad ones, don’t repeat them, and make the best that you can out of them.

There are a few basic rules for walking the path between productive mistakes and unproductive failure.

1. Make Cheap Mistakes

Not everything worth doing is worth doing well--at least at first. You need to start small on each new project and be ready to scale swiftly if it works or abandon it as soon as the handwriting is on the wall. But be selective-don’t try to do things cheaply that you shouldn’t do at all.

2. Don’t Be Reluctant to Change Your Mind

If you’re headed in the wrong direction, the first order of business is to stop. When conditions have changed, adhering to the original plan is foolish. To stick with a mistake is actually much worse than making it in the first place, because it only worsens the situation. In order to survive in this hyper-competitive world, you’ve got to be fast and flexible.

3. Don’t Dwell on the Past

It’s always O.K. to admit you’ve made a mistake. Make ‘em. Admit ‘em. Correct ’em. Forget ‘em. A short memory and some in-game amnesia are critical. If you’re worrying about the past, you’ve got a good chance of screwing up the future. You can’t water yesterday’s crops. So move on.

4. Distinguish Mistakes from Systemic Problems

The best companies understand the very crucial distinction between mistakes (errors that happen once) and systemic problems (errors that happen over and over again). They track and aggregate these occurrences to uncover patterns in them and to eliminate the causes. Mistakes will always happen, but the same mistakes shouldn’t happen over and over again.

5. Be a Big Boy or Girl

Don’t try to hide a mistake or cover it up - admit it and get to fixing it. Show some remorse and make sure that people know you’re taking it seriously. Let the appropriate people know it won’t happen again. Don’t waste your breath blaming others; you’ll need that breath to say “I’m sorry”--and then get back to work and get over it.